Synthesis, characterization, and NMR studies of 1,2,3-triazolium ionic liquids: a good perspective regarding cytotoxicity
Ionic liquids (ILs) have been extensively studied and are considered green solvents capable of replacing traditional organic solvents. In this study, seven 1,2,3-triazolium derivative ILs have been synthesized. In order to study the effect of the cation nature on the ILs cytotoxicity, their structures were first identified by 1H, 13C NMR 1D, and 2D spectroscopy. DFT calculations have also been performed in a way to help to provide an insightful structural analysis from 13C NMR spectroscopy. The comparison made with the NMR experimental shifts was quite important to show that the 1,2,3-triazolium derivatives have the expected structure shown here. The in vitro cytotoxicity of ILs toward macrophages showed that among the compounds tested, five did not exhibit expressive cytotoxicity on mammalian cells. Besides the well-established relationship between the carbonic chain size of the cation and the cytotoxicity, the log P of the compounds predicts that the toxicity increases with the size of the carbon chain, demonstrating that the most cytotoxic compound is also the most lipophilic one. The low cytotoxicity effect of ILs on mammalian cells points to their potential application in large-scale by industry.
KeywordsIonic liquids DFT calculations NMR Lypophilia
The authors wish to thank FAPEMIG (Process APQ-03830-16 and APQ-02068-14), CNPq, and CAPES for financial support. Also, LASC, ESC, and ADS would like to thank CNPq for the fellowship grant.
- 4.Khan SS, Hanelt S, Liebscher J (2009) Versatile synthesis of 1, 2, 3-triazolium-based ionic liquids. ARKIVOC 12:193–208Google Scholar
- 7.Anastas PT, Warner JC (2000) Green chemistry: theory and practice. Oxford University Press, New York, p 132Google Scholar
- 12.Yacob Z, Liebscher J (2011) 1,2,3-Triazolium salts as a versatile new class of ionic liquids. In: Handy S (ed) Ionic liquids - classes and properties. IntechOpen, London, pp 3–18Google Scholar
- 24.Carmo AML, Stroppa PHF, Corrales CNR et al (2014) Synthesis of 1,2,3-triazolium-based ionic liquid and preliminary pretreatment to enhance hydrolysis of sugarcane bagasse. J Braz Chem Soc 25:2088–2093Google Scholar
- 29.Ekwall B, Silano V, Paganuzzi-Stammati A, Zucco F (1990) Toxicity tests with mammalian cell cultures. In: Bourdeau P et al (eds) Short-term toxicity tests for non-genotoxic effects. Wiley, New YorkGoogle Scholar
- 41.Barros CL, De Oliveira PJP, Jorge FE et al (2010) Gaussian basis set of double zeta quality for atoms Rb through Xe: application in non-relativistic and relativistic calculations of atomic and molecular properties. Mol Phys 108:1965–1972Google Scholar
- 43.Frisch MJ, Trucks GW, Schlegel HB et al (2010) Gaussian 09 revision C.01. Gaussian Inc., WallingfordGoogle Scholar